Fused 3-phenyltetramic acid derivatives having herbicidal action

Abstract

and to the use of these compounds for controlling weeds and weed grasses in crops of useful plants.

1 . Compound of formula (I) 
       
         
           
           
               
               
           
         
       
       or an agrochemically acceptable salt thereof in which
 X represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkoxy or halogen; 
 Y represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkoxy or halogen; 
 W represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogen or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from the group consisting of C 1 -C 3 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, hydroxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy and halogen; 
 U and V in each case together form a seven-membered ring of the T 1 -T 4  type, 
 
       
         
           
           
               
               
           
         
         
           where Z represents an oxygen atom, a group —S(O) n — or a group —N(OR 1 )—; 
         
         n represents 0, 1 or 2; 
         R 1  represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkanoyl; 
         G represents hydrogen, a removable group L or a cation E, where L represents one of the radicals below 
       
       
         
           
           
               
               
           
         
         R 2  represents C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl; 
         R 3  represents C 1 -C 4 -alkyl; 
         R 4  represents C 1 -C 4 -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro or cyano; 
         R 5  and R 5′  each independently of one another represent methoxy or ethoxy; 
         R 6  and R 7  each independently of one another represent methyl, ethyl or phenyl or together form a saturated 5-, 6- or 7-membered ring or together form a saturated 5-, 6- or 7-membered heterocycle having an oxygen or sulfur atom; 
         E represents an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium, an ion equivalent of a transition metal, a magnesium halogen cation or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms are replaced by identical or different radicals from the groups C 1 -C 5 -alkyl, C 1 -C 6 -alkoxy or C 3 -C 7 -cycloalkyl, which may in each case be substituted one or more times with fluorine, chlorine, bromine, cyano, hydroxy or be interrupted by one or more oxygen or sulfur atoms, or a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo[2.2.2]octane (DABCO) or 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU), or a heterocyclic ammonium cation, for example in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methyl sulfate, or a sulfonium ion. 
       
     
     
         2 . Compound of formula (I) or an agrochemically acceptable salt thereof according to  claim 1 , wherein X represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 3 -haloalkoxy or halogen. 
     
     
         3 . Compound of formula (I) or an agrochemically acceptable salt thereof according to  claim 1 , wherein Y represents C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 3 -haloalkoxy or halogen. 
     
     
         4 . Compound of formula (I) or an agrochemically acceptable salt thereof according to  claim 1 , wherein W represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogen or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from the group consisting of C 1 -C 3 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy and halogen. 
     
     
         5 . Compound of formula (I) or an agrochemically acceptable salt thereof according to  claim 1 , wherein U and V in each case together form a seven-membered ring of the T 1 -T 4  type, 
       
         
           
           
               
               
           
         
       
       where Z represents an oxygen atom, a group —S(O) n — or a group —N(OR 1 )—,
 n represents 0, 1 or 2, and 
 R 1  represents C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkanoyl. 
 
     
     
         6 . Compound of formula (I) or an agrochemically acdeptable salt thereof according to  claim 1 , wherein G represents hydrogen, a removable group L or a cation E, where L represetns one of the radicals below 
       
         
           
           
               
               
           
         
         R 2  represents C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, 
         R 3  represents C 1 -C 4 -alkyl, 
         R 4  represents C 1 -C 4 -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from the group consisting of halogen and C 1 -C 4 -alkyl, 
         R 5  and R 5′  represent methoxy or ethoxy, 
         R 6  and R 7  each independently of one another represent methyl, ethyl or phenyl, and 
         E represents an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium, an ion equivalent of a transition metal, a magnesium halogen cation or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms are replaced by identical or different radicals from the groups C 1 -C 5 -alkyl, C 1 -C 6 -alkoxy or C 3 -C 7 -cycloalkyl, or a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU) or choline. 
       
     
     
         7 . Compound of formula (I) or an agrochemically acceptable salt thereof according to  claim 1 , wherein
 X represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 3 -haloalkoxy or halogen,   Y represents C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 3 -haloalkoxy or halogen,   W represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogen or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from the group consisting of C 1 -C 3 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy and halogen,   U and V in each case together form a seven-membered ring of the T 1 -T 4  type,   
       
         
           
           
               
               
           
         
       
       where Z represents an oxygen atom, a group —S(O) n — or a group —N(OR 1 )—,
 n is 0, 1 or 2, 
 R 1  represents C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkanoyl, 
 G represents hydrogen, a removable group L or a cation E, where L represents one of the radicals below: 
 
       
         
           
           
               
               
           
         
         R 2  represents C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl, 
         R 3  represents C 1 -C 4 -alkyl, 
         R 4  represents C 1 -C 4 -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from the group consisting of halogen and C 1 -C 4 -alkyl, 
         R 5  and R 5′  represent methoxy or ethoxy, 
         R 6  and R 7  each independently of one another represent methyl, ethyl or phenyl, 
         E represents an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium, an ion equivalent of a transition metal, a magnesium halogen cation or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms are replaced by identical or different radicals from the groups C 1 -C 5 -alkyl, C 1 -C 6 -alkoxy or C 3 -C 7 -cycloalkyl, or a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU) or choline. 
       
     
     
         8 . Herbicidal composition comprising a compound of formula (I) according to  claim 1  or an agrochemically acceptable salt thereof, and optionally an agrochemically acceptable carrier, diluent and/or solvent. 
     
     
         9 . Herbicidal composition according to  claim 8 , comprising at least one further pesticidally active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators. 
     
     
         10 . Herbicidal composition according to  claim 8 , comprising a safener. 
     
     
         11 . Herbicidal composition according to  claim 8 , comprising a further herbicide. 
     
     
         12 . Method for controlling undesired plant growth, where the compound of formula (I) or an agrochemically acceptable salt thereof according to  claim 1  is applied to the plant to be controlled, plant parts, plant seeds or an area on which undesired plant growth takes place. 
     
     
         13 . Method according to  claim 12 , where the undesired plant growth is selected from grasslike monocotyledonous weeds. 
     
     
         14 . Method according to  claim 12 , where the plant growth of resistant grasses in useful plants is controlled, and where the herbicidal composition is applied to the weed to be controlled. 
     
     
         15 . Method according to  claim 14 , where the useful plant is selected from wheat, barley, rye, oats, rice, sugar cane, soybean, rapeseed, sunflower and corn. 
     
     
         16 . A compound of formula (I) or an agrochemically acceptable salt thereof according to  claim 1  for controlling harmful plants. 
     
     
         17 . A compound according to  claim 16 , wherein the compound of the formula (I) or an agrochemically acceptable salt thereof is used for controlling one or more harmful plants in a crop of useful plants. 
     
     
         18 . A compound according to  claim 16 , wherein the useful plants are transgenic useful plants.